(S)-benzyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-2-(methoxycarbonylamino)propanoate → HCID 178502274, compound

HRID 68281Notes

Reaction equation

HRID 68281 reaction equation
C([N:8]1[CH:12]=[C:11]([CH2:13][C@H:14]([NH:25][C:26]([O:28][CH3:29])=[O:27])[C:15]([O:17]CC2C=CC=CC=2)=[O:16])[N:10]=[N:9]1)C1C=CC=CC=1>CO.[Pd]>[CH3:29][O:28][C:26]([NH:25][C@@H:14]([CH2:13][C:11]1[N:10]=[N:9][NH:8][CH:12]=1)[C:15]([OH:17])=[O:16])=[O:27]

Participants

4

Reactant 1

HCID 71182684(S)-benzyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-2-(methoxycarbonylamino)propanoate

Product 1

HCID 178502274HCID 178502274, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-benzyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-2-(methoxycarbonylamino)propanoate (502 mg, 1.11 mmol) was hydrogenated in the presence of Pd—C (82 mg) in MeOH (5 mL) at atmospheric pressure for 12 h. The mixture was filtered through diatomaceous earth (Celite®) and concentrated in vacuo. (S)-2-(methoxycarbonylamino)-3-(1H-1,2,3-triazol-4-yl)propanoic acid was obtained as a colorless gum (266 mg, 111%) which was contaminated with ca. 10% of the methyl ester. The material was used as is without further purification. 1HNMR (400 MHz, DMSO-d6) δ 12.78 (s, br, 1H), 7.59 (s, 1H), 7.50 (d, J=8.0 Hz, 1H), 4.19-4.24 (m, 1H), 3.49 (s, 3H), 3.12 (dd, J=4.8 Hz, 14.9 Hz, 1H), 2.96 (dd, J=9.9, 15.0 Hz, 1H). LCMS: Anal. Calcd. for C2H10N4O4: 214. found: 215 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth (Celite®)
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-071da277ea30492f9755972d5e8511ec
Source dataset
uspto-grants-2014_09
Patent number
US08822444B2

Reaction notes

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